1. Field of the Invention
This invention relates to 1-aryl-1-[.alpha.-triazolyl)alkyl]-1-silacycloalkanes as represented as formula I, their preparation, and their use in controlling fungal diseases of living plants. ##STR2##
wherein R.sub.1 can be 4- or 2,4-substituted phenyl such as 4-fluorophenyl, 4-chlorophenyl, 4-ethoxyphenyl, 4-methoxyphenyl, 4-trifluoromethylphenyl, biphenyl, 2,4-difluorophenyl, and 2,4-dichlorophenyl and R.sub.2 can be hydrogen or methyl and n is 4 or 5.
2. Description of the Prior Art
Since the late 1960's, the derivatives of azoles have been known to be useful for the control of plant diseases (M. Plempel, K. Bartmann, K. H. Bichel and Regel, Deutsche Med. Wochenschrift, 4, 1356-1364 (1969)). U.S. Pat. No. 3,692,798 discloses later the organosilylimidazoles of the following formula: ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 can be lower alkyl and phenyl. It is stated that these compounds are useful as antimicrobial agents.
German Pat. No. DE 3,000,140 discloses silyl ethers of the formula: ##STR4## wherein Ar can be substituted phenyl, X can be CH or N, and R can be phenyl or lower alkyl. It is taught that organosilyl imidazoles or triazoles are useful as agricultural fungicides.
U.S. Pat. No. 4,510,136 discloses organosilyl group substituted at beta carbon to triazole ring represented by the following formula: ##STR5## wherein R.sub.1, R.sub.2, and R.sub.3 can be independently lower alkyl or substituted phenyl, and Q.sub.1 and Q.sub.2 can be independently H or CH.sub.3. It is stated that the organosilyl triazoles have strong fungicidal activities and can be used to control plant fungus diseases.
The organosilyl triazoles with aromatic substituents on silicon have better fungicidal activities than the organo-silyltriazoles with alkyl substituents on silicon. The triazoles with phenyl groups on silicon, having fluorine, trifluoromethyl, ethoxy, or phenyl substituent at para position show better activities than those having chloro or methyl substituent at para position.
Japanese Pat. Pub. No. 63-5092 discloses organosilyl bistriazoles of the following formula: ##STR6## wherein X can be H, halogen, alkoxy, phenyl, substituted phenyl with halogen or lower alkyl group. It is taught that the organosilyl bistriazoles have fungicidal activities.
German Pat. DE 3,723,246 discloses organosilyl compounds having triazole and thiophene group of the formula: ##STR7## wherein X can be alkyl or halogen and R can be phenyl or substituted phenyl.
U. S. Pat. Nos. 4,530,922 and 4,729,982 also disclose the triazole compounds which are similar to the compounds disclosed in U.S. Pat. No. 4,510,136 except that alkenyl or ethynyl groups substitued on silicon instead of the methyl group. It is also stated that the compounds disclosed in the patents having thiols or thiocyanide groups substitued on the triazole ring are active.
U.S. Pat. No. 5,235,061 also discloses that (1H-1,2,4-triazolyl)disilaalkanes as represented by the following formula have fungicidal activities and can be used to control plant fungus diseases: ##STR8## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 can be independently lower alkyl, vinyl, allyl, benzyl, or substituted phenyl such as parafluorophenyl, para-chlorophenyl, para-ethoxyphenyl and biphenyl.